Book Luxury Short Stay Rentals in Old Windsor

We selected the 5540 homes worth renting in this location!

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Home spotlights in Old Windsor

Mane Character

Mane Character

  • 4 guests

  • 2 bedrooms

Billingshurst, West Sussex

One of a collection of three cottages on a thirteen-acre working farm in West Sussex, this home is nowhere near as rustic as these details might suggest. Step behind the front door and you'll find an interior that's contemporarily styled with a few quirky touches.

What a Day for a Daydream

What a Day for a Daydream

  • 2 guests

  • 1 bedrooms

Hascombe, Godalming

Country escapes don’t get much more idyllic than this beautifully renovated studio barn in the village of Hascombe. Surrounded by two Areas of Oustanding Natural Beauty – the South Downs and the Surrey Hills – you’re in the perfect spot to enjoy countless walking trails and stunning scenery galore.

Gather & See

Gather & See

  • 10 guests

  • 5 bedrooms

Windsor, Berkshire

This home is a great option for groups looking for a centrally-located stay in Windsor. By day, you can enjoy all that the city has to offer on foot – Windsor Castle is a short walk away and you’ll find the river is within easy reach.

Britannia Jewel

Britannia Jewel

  • 5 guests

  • 3 bedrooms

Windsor, Berkshire

Sitting on a quiet residential street in central Windsor, this beautiful upper maisonette offers a warm and welcoming base for those looking to experience the town’s rich and royal history, as well as the delights of nearby Eton, Ascot and Legoland. Laid out over three floors, you’ll find plenty of space to socialise as well as opportunities to steal yourself await for some relaxing privacy.


We selected the top 3% holiday homes in Old Windsor Short Stay Rentals

Explore the 5540 most perfect homes in our collection

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Most popular homes in Old Windsor

River Rest

River Rest

  • 2 guests

  • 1 bedrooms

Marlow, England

Skindles

Skindles

  • 5 guests

  • 2 bedrooms

Maidenhead, Berkshire

The Saddler's Rooms

The Saddler's Rooms

  • 6 guests

  • 3 bedrooms

Hampshire, England

Hang on to Your Hat

Hang on to Your Hat

  • 4 guests

  • 2 bedrooms

Dunstable, Central Bedfordshire

The Windsor Lookout

The Windsor Lookout

  • 6 guests

  • 3 bedrooms

Windsor, Berkshire

A Day at the Regatta

A Day at the Regatta

  • 14 guests

  • 4 bedrooms

Dorney, Buckinghamshire

It's Aboat Time

It's Aboat Time

  • 6 guests

  • 3 bedrooms

Chertsey, Surrey

A King's Retreat

A King's Retreat

  • 8 guests

  • 4 bedrooms

Sunninghill and Ascot, Berkshire

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Frequently asked questions

Browse our curated collection of Short Stay Rentals in Old Windsor. From impeccable interior design and chef-worthy kitchens, to fully furnished bathrooms and the inclusion of all linens, the homes in our collection come complete with everything you need. Each of the Old Windsor luxury short stay apartments in our collection has been expertly reviewed to ensure the quality standards you can trust, so book today to enjoy a getaway to remember. And should you need any assistance, our friendly team of experts are here to help you find the perfect home.

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